CAS 1491-59-4|Rhinolitan|Rhinofrenol|Oxymethazoline|Nezeril|Duration 12 Hour Nasal Spray|Oximetazolinum|Oxymetozoline|Dristan Long Lasting Mentholated Nasal Spray|Visine L.R|Drixoral Nasal Solution|...

General Information

Structure

Molecular Formula

C₁₆H₂₄N₂O

Molecular Mass

260.37456

Exact Mass

260.1888634

Charge

InChI

InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)

InChIKey

WYWIFABBXFUGLM-UHFFFAOYSA-N

Canonic Smiles

Cc1cc(c(c(c1CC1=NCCN1)C)O)C(C)(C)C

Isomeric Smiles

Oc1c(C(C)(C)C)cc(c(c1C)CC1=NCCN1)C

Calculated Properties

JChem

LogD (pH = 7.4)

1.20

LogD (pH = 5.5)

1.06

Log P

3.03

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

10.15

Polar Surface Area

44.62

Polarizability

30.65

Molar Refractivity

79.80

LOG S

-2.99

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

RhinolitanRhinofrenolNezerilDuration 12 Hour Nasal SprayDristan Long Lasting Mentholated Nasal SprayVisine L.RDrixoral Nasal SolutionGenasal Nasal Spray Up to 12 Hour ReliefAfrin Sinus 12 Hour Nasal SprayNavasinOcuClearNeo-Synephrine 12 Hour SprayNostrilla 12 Hour Nasal DecongestantSinerolAfrin Original 12 Hour Nasal SprayDuramist Plus Up To 12 Hour Nasal Decongestant SprayHazolNafrineVisine L.R.Vicks Sinex 12 Hour Ultra Fine Mist for Sinus ReliefAfrin Original 12 Hour Nose DropsAfrinAfrin Cherry 12 Hour Nasal SprayDristan Long Lasting Nasal MistAfrin Original 12 Hour Pump MistNasivineVicks Sinex 12 Hour Nasal SprayAfrin Extra Moisturizing 12 Hour Nasal SprayNasal Relief 12 Hour Nasal SprayIliadinOxylazineNavisinAfrin, Dristan12-hrnasalspray, Ocuclear, Drixine

Synonyms

OxymethazolineOximetazolinumOxymetozolineoxymetazoline hydrochloride crystallineOxymetazoline2-(3-hydroxy-2,6-dimethyl-4-tert-butylbenzyl)-2-imidazoline6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenoloxymetazoline2-(4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol

IUPAC Traditional name

oxymetazoline

IUPAC name

6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol 6-tert-butyl-3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-2,4-dimethylphenol

International Nonproprietary Name (INN)

oxymetazolineoxymetazolinumoxymetazolina

Names and Identifiers

Registration numbers

CAS Number

1491-59-4

PubChem CID

4636

PubChem SID

46505622160964274223440378

Chemspider ID

4475

ATC CODE

S01GA04R01AB07R01AA05

DrugBank ID

DB00935

Unique Ingredient Identifier

Wikipedia Title

KEGG ID

IUPHAR ligand ID

CHEMBL

UniProt Database

Q8JG69O01670Q8JG70Q90WY4P08913O77408P18089

MetaboLights Database

MTBLS417MTBLS2145MTBLS2349

Patent number

DE1117588

PubMed Citation Links

104870002367907723988443211774874003266

ACToR Database

CompTox Database

KEGG DRUG Database

HMDB Database

Reactom Database

R-HSA-9623384R-HSA-390641

SureChEMBL Database

SCHEMBL24301

Drug Central Database

BindingDB Database

CHEBI ID

LINCS Database

Reaxys Registry

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

3.4

Melting Point

301.5°C (574.7°F)

Pharmacology Properties

Legal Status

GSL (UK)

OTC (US)

Half Life

5-6 hours

Pregnancy Category

Product Information

Purity

97%

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00935

Drug Groups

approved

Description

A direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)

Indication

For treatment of nasal congestion and redness associated with minor irritations of the eye

Pharmacology

Oxymetazoline a adrenergic alpha-agonists, direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion The sympathomimetic action of oxymetazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (up to 12 hours), gentle and decongesting effect. Oxymetazoline elicits relief of conjunctival hyperemia by causing vasoconstriction of superficial conjunctival blood vessels. The drug's action has been demonstrated in acute allergic conjunctivitis and in chemical (chloride) conjunctivitis.

Affected Organisms

Humans and other mammals

External Links

• [Wikipedia]

• [Drugs.com]

A member of the class of phenols that is 2,4-dimethylphenol which is substituted at positions 3 and 6 by 4,5-dihydro-1H-imidazol-2-ylmethyl and tert-butyl groups, respectively. A direct-acting sympathomimetic with marked alpha-adrenergic activity, it is a vasoconstrictor that is used (generally as the hydrochloride salt) to relieve nasal congestion.

Molecule Details

References

PubChem Literature

No Data Available

Click here to submit data

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties